Processes for the reaction of silanic hydrogen-bonded compounds with unsaturated hydrocarbons



2,851,473 Patented Sept. 9, 1958 ice PROCESSES FGR TEE REACTION OFSILANIC HYDROGEN-BUNDED COMPOUNDS WHTH UN- SATURATED HYDROCARBONS NoDrawing. Application December 23,1955

' 'Eaerial No. 554,938

16 Claims. c1. 260-4481) George H. Wagner, Jr., Kenmore, poration,

This invention relates in general to improved methods or processes forthe production of organosilicon compounds, i. e., organic derivatives ofsilicon containing carbon to silicon bonds. Morerparticularly, theinvention contemplates the provision of unique syntheses for promotingreactions between silane compounds of the type containing at least onesilanic hydrogen bond (ESl-H), with unsaturated hydrocarbons, whereinthe reactions are catalyzed by means of a new and improved form ofheterogeneous or multicomponent catalyst consisting of platinum andgamma alumina.

It has been proposed heretofore (U. S. 2,632,013 to Wagner and Strother)to catalyze the reactions between ethylenic or acetylenic hydrocarbonsand silanes containing silanic hydrogen, by means of platinum, platinumblack, platinized silica gel, or platinized asbestos. It is also known(U. S. 2,637,738 to Wagner) that platinum supported on finely-dividedcharcoal provides an active and selective catalyst for the addition ofsilanes of the general class described to aliphatic unsaturatedcompounds. While these known forms of catalysts are, for the most part,effective for the purpose intended, our investigations have demonstratedthat in at least certain reactions of the generic class defined they areeither without effect or are readily susceptible to poisoning orso-called catalytic fatigue, becoming stopped-off, so to speak, therebynecessitating intermittent regeneration through the addition of furtherquantities of catalyst. It is presumed that this failure of therelatively cheaper and, therefore, preferred multicomponent catalysts,such as the charcoal-supported platinum catalyst, is influenced in someunknown manner by the charcoal support, possibly by reason of theformation of obstructive films due to a distorting action exercised bythe carrier on the electric fields of the catalysts active centers,since fatigue or poisoning of platinum, per se, is not necessarilyinduced under the same conditions of operation.

As a result of our detailed investigations of the aforementionedphenomena, we have found that a heterogeneous catalyst consisting ofplatinum deposited on the gamma allotrope of alumina not only avoids thefatigue factor characteristic of known catalysts when employed under thesame conditions, but provides an outstandingly effective agent forcatalysis, in general, of the reactions between the systems C=C or C50and SiH, producing increased yields of the products of such reactionsand permitting substantially continuous or flow-type operations at lowerpressures and temperatures than have been possible heretofore.

The exact mechanism underlying the unique effectiveness ofplatinum-gamma alumina as a catalyst in reactions of the general classdescribed is not known, but it is believed to be related in some mannerto the cubic crystal structure of the gamma allotrope of alumina, sincethe alpha allotrope of alumina, which is hexagonal in crystal structure,when employed in conjunction with platinum in the form of aheterogeneous catalyst produces only normal or expected catalyticactivity. While 2 the gamma alumina component of our catalyticcomposition may be viewed in one sense as a carrier or support for theplatinum component, the terms carrier and support actually denote aninert material which functions solely as a physical holder for acatalytic substance. It has been postulated that when a so-calledcarrier or support increases or decreases the rate of reaction duringcatalysis, or directs the rate of reaction in any manner, it is nolonger simply a carrier. In view of the unexpected results obtainedthrough the use of gamma alumina in combination with platinum accordingto processes of our invention, and, in the absence of any provenscientific explanation of the mechanism underlying these results, weprefer to define the platinum-gamma alumina composition as amulticomponent or heterogeneous catalyst rather than a simplecarrier-supported catalyst within the meaning assigned above. Apart fromyielding a cheaper substitute for the unexposed mass of a plain platinumcatalyst and the apparent protection from poisons afforded the platinumby the gamma alumina, the function of the gamma alumina with respect tothe platinum remains unknown to us and the overall superiority of thecatalyst, as will be developed more fully in the following passages,might well be due to a combination of factors including, for example,larger contact area or. more equal distribution of the platinum,

alteration of the adsorption characteristics and sensitivity topoisoning of the platinum, counteraction of loss of catalytic activityat higher temperatures, etc.

The gamma alumina component. of the catalyst employed in the processesof the invention may be prepared in any suitable manner, such, forexample, as by the thermal decomposition of ammonium alum, [A1 (NH (SO24H 0], at a temperature within the range 1000l050 C., or by dehydrationof aluminum hydroxide at a temperature within the range 900l C., etc.The combined catalyst may be prepared in accordance with a number ofdifferent conventional procedures followed in the preparation ofplatinum catalysts in general. For our investigations, we employed ahigh purity (99.99+%) gamma alumina powder and formed a thick slurrywith an aqueous solution of platinic chloride adjusted with respect toplatinum content to provide the amount of platinum desired in the finalproduct. The I resulting slurry was dried at C. and then heated at 500C. in a reducing atmosphere (such as hydrogen or annealing gas) untilthe platinum content of the plat-inic chloride was reduced to theelemental state.

The utility of the platinum-gamma alumina catalyst in v promotingreactions between silanes containing at least one silanic hydrogen bondand unsaturated hydrocarbons, appears to be general. Thus, the genericclass of operative compounds may be defined by the following formula:

RaSiI-I X wherein a=0, l, or 2; b=1, 2 or 3; a +b=4 or less; R=ahydrocarbon group; and

X=halogen or alkoxy.

Typical starting materials within the foregoing definition which may beemployed in processes of the invention are the partially chlorinatedsilanes, such as, monochlorosilane (SiH Cl); dichlorosilane (SiH Cl andtrichlorosilane(SiHCl alkyland alkoxy-substituted silanes andchlorosilanes, such as methyl. dichlorosilane CH iH a the very lowconcentrations of platinum required in the catalyst of the invention inorder to obtain high yields at relatively lower pressures andtemperatures and in shorter reaction times than have been possibleheretofore with the conventional or standard forms of catalystscustomarily employed in this general type of reaction. The results ofthese experiments are set forth in tabulated form in Table 11 below. Itshould be noted that these data also further demonstrate theinelfectiveness of platinum-alpha alumina as a catalyst in reactions ofthe general class described. In all of the experiments, 100 millilitersof liquid dichlorosilane and the respective catalysts were reacted withethylene in a 300 cc. reactor.

TABLE I1 Reactions of dichlorosilane 1 and ethylene catalyzed withplatinum-gamma alumina and platinum-alpha alumina Pressure, p. s. 1.Temp, 0. Product (Percent by Weight) Time, Hr. Start Max. Start Max.EtSiCla EtgSiCli Et SiCl 0.5 g. of 5.1 370 830 149 152 1. 3 0.5 g. of4.8 420 700 151 228 0.3 7. 1 90. 6 2 3 0.1 g. of 4.8 400 700 149 202 0.5 7. 2 90. 4 2. 4 0.1 g. of 4.8 300 600 132 208 0.4 5.8 91. 7 2. 5 0.1g. 011.0 280 630 132 205 0. 3 4. 4 93. 4 2. 2 0.2 g. of 0.05%Pt-gamma-AlzOz 280 850 134 172 0.8 4. 8 93. 8 1. 4

1 Containing small amounts of HSiOla and HsSlCl.

was conducted in a series of experiments utilizing the catalyst of theinvention, platinized alpha alumina and a variety of other platinizedceramic carriers. Whereas the platinized alpha alumina and all othercatalysts tested failed to induce ethylation, the platinum-gamma aluminaproduced excellent yields as shown in tabulated form in Table I below.In this series of experiments, 1.0 percent by weight of platinum wasdeposited on the respective carriers in conventional fashion and 0.1gram of each of the resulting catalysts and 100 milliliters of liquiddichlorosilane were heated to 130 C. in a reaction vessel of 300 cc.capacity. Ethylene was then admitted to a partial pressure of 300 poundsper square inch (total pressure 600 p. s. i.) and the extent of reactiondetected by ethylene absorption and temperature rise.

TABLE I Comparison platinum-gamma alumina, platinum-alpha alumina, andother platinized ceramic carriers in the ethylation of dichlorosilaneSupport Observations (1) Silica (Si-O-Lite) (2) Bis Ethyl Gel (asiloxane powder of high surface area).

(3) Silicon oxyhydride (4) Alpha Alumina (high surface area).

(5) MgO90% -Alq03 (Spinel Boule Powder).

(6) Polyvinyl Siloxane Powder.

(7) Gamma Alumina No reaction even after 1 hour at 1,000 p. S. i.

Small initial reaction at 600 p. s. i. No further reaction at 1,000

p. s. 1. Same as (2) above. Same as (2) above.

Moderate initial reaction which stops after mins. at 900 p. s. i. At 150C. and 1,100 p. s. i. almost complete ethylation takes place.

Small initial reaction at 600 p. s. i. No appreciable further reactionat 170 C. and 1,000 p. s. i.

Very pronounced or strong reaction at 600 p. s. i. Self-sustaining.Complete ethylation in minutes.

Of particular significance with respect to the data presented in theforegoing tables, and, characteristic of one of the more importantadvantages of the platinumgamma alumina catalyst, is the fact that thereactions as catalyzed with this composition are completelyself-sustaining. Heretofore, high dichlorosilane content alkylationscould only be effected on a batchwise basis in autoclave-type reactionvessels wherein it is possible to make additions of catalyst, as, forexample, platinized charcoal, to regenerate the reaction whenever itstopped due to catalytic fatigue or poisoning. The processes of theinvention, on the other hand, may be effected in continuous or flow-typealkylation units owing to the unique catalytic properties of theplatinum-gamma alumina catalyst. Furthermore, because of the higherreaction rates obtainable with our catalyst and the total absence ofpoisoning effects thereon, the completeness of the reactions obtained inthe continuous-type units renders it unnecessary to recycle reactants inthe manner practiced heretofore, thereby resulting in a substantiallowering of product cost.

The value of the platinum-gamma alumina catalyst in the continuousreaction of acetylene with trichlorosilane for the production ofvinyltrichlorosilane has also been demonstrated. Thus, this reaction, aswell as the corresponding ethylene reaction, when catalyzed withplatinized charcoal frequently yield erratic results. It was found thatthis variation in activity is apparently a function of the amount ofdichlorosilane present in the trichlorosilane used as a startingmaterial in that reasonably good reactions were obtained when thedichlorosilane content of the trichlorosilane was less than one percent(1.0%), but poor results were obtained when the dichlorosilane contentrose above this figure. Specifically, it was found that in the reactionas catalyzed with platinized charcoal, the presence of one percent(1.0%) or more of dichlorosilane in the trichlorosilane caused adecrease in conversion from fifty percent (50%) to twentyfive percent(25%). Upon substituting platinum-gamma alumina as catalyst in thereaction, these variations were completely eliminated and a markedincrease in activity was obtained either in the presence ofdichlorosilane or when the dichlorosilane content was very low (lessthan 1.0%). Conversions as high as ninety percent were obtained in thepresence of one and three-tenths percent (1.3%) dichlorosilane in thetri-functional starting compound, when employing platinum-gamma aluminaas'catalys't. "Onthebasi'sbf these observations, it will be readilyapparent that a further irriportant advantage of the processes 'of'the'invention'resides in the' fact that crude trichlorosilane' maybeutilized in these reactions when catalyzed with platinum-gammaalumina, whereas formerly a good rectification was essential for highyields.

heresults of the "foregoing tests are summarized in Tables II I and IV,below. f The equipment for these continuous flow reactions consisted ofa vertical. single-pass tubular reac 'on cham ber (1.0" x 20.0)surrounded by t jacket for temperature control, an agitator-typelfeedltankfor the chlorosilane-catalyst suspensions, a compressorequipped with pressure and flow controls. for th e acetylene feed and asimple collection tank for the'reac'tion lproductsgf'lhe' conditions ofreaction were essentially "the same for both catalysts. The flow rate ofthejchloros'ilanein the, reactions catalyzed with platini'zedjc'harcoal(Table III) was five to eight (5-8) gallonsper hourfwhile a flow rate offive to twelve (5-12) gallons 'per hour was' employed in the reactionscatalyzed with platinum-gamma alumina (Table IV).

Four '(4) grams of platiuized 'charcoal'containing 1.0 percent byweightplatinum, and three (3) grams of platinum-gamma alumina containing 1.0percent by weight platinum Were used, per gallon of trichlorosilanereacted, except where noted otherwise. The reactions were conducted atapressur'e" of 350 pounds per square inch and at temperatures within therange 150-250 C., with ten percent (10%) nitrogen being used as diluentfor runs with both catalysts, although subsequent tests demonstratedthat this data show that the percentage conversion of tric hlorosilaneto vinyltrichlorosilane ranged from twenty-five to sixty percent(25-60%) forplatinized charcoal, as compared to sixty to ninety percent(60-90%) for platinumgamma alumina.

TABLE III Continuous flow reactions of acetylene and trichlorosilanecatalyzed with platinized charc oal Feed Purity in Mole Percent ProductComposition (Percent by Wt.) Run 11281012 BS1013 S1014 CH2=OHSiCl3Heavies Averages.- 1 45.0 1 8. 0

l Remainder unreacted lights. 1

TABLE IV Continuous flow reactions of acetylene and triehlorosilanecatalyzed with platinum-gamma alumina Feed Purity in Mole PercentProduct Composition was not essential for the reactions", catalyzed withplatinum-gamma alumina. The tabulated A similar comparisonwas madebetween platiuized charc'oal'and platinurii 'ga'mma alumina in thecontinuous reaction of ethylene with true mixtures of dichlorosilane andtrichlorosilane and the results of these experiments areset forth inTables V and VI below. The equipment and general procedure employed inthese tests were the same as those described in connection with theacetylene reactionsof Tables III and IV. The flow rate of themixedchlorosilanes in the reactions catalyzed with platinizedcharc'oal(Table V) was three to six (3-6) gallons per hour, while a flow rate ofeight and one-half to fourteen 8.5-14) gallons per hour was employed inthe reactions catalyzed with platinum-gamma alumina (Table VI). Theseparate platiuized charcoal catalysts designated A and B inTable V,were a commercial prodnet and a laboratory-prepared product,respectively, each containing five percent (5.0%) platinum, and bothwere' employed at rate of four to five (4-5) grams per gallon of mixedchlorosilanes. The platinum-gamma alumina catalystcmployed in thereactions of Table VI contained one percent (1.0%) platinumand was usedat a rate of three (3 grams per gallon of mixed chlorosilanes. A widerange of pressures were employed, without success, in an attempt toobtain reactions with the platiuized charcoal, whereas for the excellentreactions obtained with platinum-gamma alumina, the optimum pressure wasfound to be 750 pounds per square inch, although they are operative overa wide range of pressures. The initial temperature for both catalystsranged between150-l60" C. with an ultimate range of only 150-190" C. forthe platiu zed charcoal catalyzed reactions, indicating lowheatofreaction, as compared to a rise in temperature up to 250?" C.,indicating excellent and rapid exothermic was obtained in any of thereactions catalyzed with the platiuized charcoal catalysts.

TABLE V Continuous flow reactions of ethylene and mixtures ofdichlorosilane and trichlorosilane catalyzed with platinized charcoal WFeed Purity Conversion of (Percent)- (Percent by Wt'.) Run Oatalyst'HzSiClz BS1013 11251012 to HzSiCls to HSiCla to EtSiHClz' Et siClgEtSiCla TABLE VI Continuous flow reactions of ethylene and mixtures ofdichlorosilane catalyzed with platinum-gamma alumina Feed PurityConversion of (Percent) (Percent by Wt.) Run HzSiCh HSiCla. HzSiClz (.01123101 to 1131013 to i EtSlHClz Et2SiCl2 'EtSiCl;

In addition to the foregoing data which illustrate the unusual activityof platinum-gamma alumina as a catalyst in the reactions for theformation of diethyldichlorosilane and vinyltrichlorosilane, excellentresults have been demonstrated, also, in the following typicalreactions, among others:

With reference to the foregoing Equations AD, in Table VII below thereare set forth data obtained in a series of static experiments involvingthese reactions which were conducted for purposes of furtherdemonstrating the general utility of the platinum-gamma alumina catalystin reactions between the systems SiH and C:C or CEC. The procedureemployed in the reactions of Table VII consisted of mixing the catalystand silicon derivative in a pressure vessel and adding the unsaturatedorganic reactant thereto at the respective pressures and temperaturesindicated. Thereafter, the reaction vessel was cooled, vented, and theresulting products analyzed. The weight-percentage yields of productsindicated in the right-hand column of Table VII do not show therelatively small quantities of lights, unreacted ingredients, and heavyfractions obtained, but these were included in calculating the yieldfigures.

TABLE VII On the other hand, in employing the platinum-gamma aluminacatalyst in accordance with the processes of the present invention, thepurity of the reaction product with respect to functionality'is exactlythe same as the purity of the starting compounds.

What is claimed is:

1. In a process for the production of organosilicon compounds thatcomprises reacting an unsaturated organic compound containing at leastone non-aromatic multiple carbon to carbon bond with a silane containingat least one silanic hydrogen bond, the improvement that comprisescatalyzing the reaction with platinum-gamma alumina.

2. In a process for the production of organosilicon compounds thatcomprises reacting an unsaturated hydrocarbon containing at least onenon-aromatic multiple carbon to carbon bond with a silane containing atleast one silanic hydrogen bond, the improvement that comprisescatalyzing the reaction with platinum-gamma alumina.

3. In a process for the production of organosilicon compounds thatcomprises reacting a compound selected from the group consisting ofunsaturated aliphatic hydrocarbons with a silane having the formula;

Reactions of Si-H and C=C 0r CEC catalyzed with platinum-gamma aluminaType of reaction (equa- Grs. of Reaction tions A-D) and Si-H 1% Pt-Unsaturated. Organic Temp, Pressure, Time, Product (Percent by Wt.)Compound Gamma Compound C. P. s. 1. Hr.

A CaH SiHCl; (400 00.).... 0.1 01H; 95-100 200 1.3 EtViSiOl: (86.7)

A OQ ESi Ch (400 cc.) 1.0 01H, 80 1.3 EtViSiCh (74.3)

A CzHsSiHClg (600 cc.) 1. 5 C 11, 80 80 1. 5 EtVlSiCh (78.8)

B IIJt 031153111011 (904 g.) 10.0 GgHsCH=OHf 200 24 BetattEtSlOlg (75.6)

(styrene) (728 g.)

ViSiHChQllA) HgSiOlq (400 cc.) 1.0 CzHz- 80 245 6 (VlSlHCl2)(37.8)

VlzSlOla (2.4)

C iSiHOh(39.0) HgSiCh (400 cc.) 6.0 03H: 55-84 125-235 6 ViqS1C1z(15.9)

(ViS1HOh) (34.0)

C H s o1" vi s iili ii ii' i 400 cc. 2 2 a a 0 80 200-280 4vnsiononronrsinoham) D (ViSLHClDn (31.1) I 03 3781015083) HSlCls (542g.) 2.0 C1OH OH -3H1 120 100-130 5 (mm chloride) {OlOzHgSlOh(35.5) (306g.)

Containing commercial inhibitor. Containing 4.8 g.di-tert.-buty1p-eresol. It is interesting to notethat activated charcoalas emwherein,

ployed in the formation of platinized charcoal catalysts causes somedisproportionation of silicon-hydrogen and silicon-chlorine bonds. Thus,when trichlorosilane is employed in reactions of the general classdescribed which are catalyzed with platinizcd char-coal, somedichlorosilane as well as some silicon tetrachloride are produced. Inthe same manner, when dichlorosilane is used some trichlorosilane aswell as some monochlorosilane are produced. We have found that suchdisproportionation does not occur when activated charcoal is absentprovided, of

a=0, 1 or 2 b=1, 2 or 3 a+b=4 or less R=a hydrocarbon group, and X is amember selected from the group consisting of halogen and alkoxy; theimprovement that comprises catalyzing the reaction with platinum-gammaalumina.

4. In a process for the production of organosilicon compounds thatcomprises reacting a compound selected from the group consisting ofalkenes and alkynes with a course,'that Friedel-Crafts type catalystsare also absent. silane containing at least one silanic hydrogen bond,the

improvement that comprises conducting the reaction in the presence ofplatinum-gamma alumina, as catalyst.

5. In a process for the production of organosilicon compounds thatcomprises reacting a compound selectedfrom the group consisting ofalkenes and alkynes with a silane containing at least one silanichydrogen bond, the improvement that comprises conducting the reaction inthe presence of elemental platinum deposited on gamma alumina, ascatalyst.

6. The process as claimed in claim 5, in which the catalyst consists ofgamma alumina and 0.05 percent to 5.0 percent by weight of elementalplatinum.

7. In a process for the production of organosilicon compounds thatcomprises reacting a compound selected from the group consisting ofalkenes and alkynes with a silane containing at least onesilicon-hydrogen bond and in which any valance of silicon not bondedwith hydrogen is bonded with a member selected from the group consistingof halogen atoms and monovalent hydrocarbon radicals, the improvementthat comprises conducting the reaction in the presence of platinum-gammaalumina, as catalyst.

8. In a process for the production of organosilicon compounds thatcomprises reacting a compound selected from the group consisting ofalkenes and alkynes with a silane containing at least onesilicon-hydrogen bond and in which any valence of silicon not bondedwith hydrogen is bonded with a member selected from the group consistingof halogen atoms and monovalent hydrocarbon radicals, the improvementthat comprises conducting the reaction on a continuous basis in thepresence of platinum-gamma alumina, as catalyst.

9. In a process for the production of organosilicon compounds thatcomprises reacting a compound selected from the group consisting ofalkenes and alkynes with a silane containing at least onesilicon-hydrogen bond and in which any valence of silicon not bondedwith hydrogen is bonded with a member selected from the group consistingof halogen atoms and monovalent hydrocarbon radicals, the improvementthat comprises conducting the reaction in the presence of elementalplatinum deposited on gamma alumina, as catalyst.

10. In a process for the production of organosilicon compounds thatcomprises reacting a compound selected from the group consisting ofalkenes and alkynes with a substance selected from the group consistingof silanes and mixtures of silanes containing at least onesiliconhydrogen bond and in which any valence of the silicon 10 notbonded with hydrogen is bonded with a member selected from the groupconsisting of halogen atoms and monovalent hydrocarbon radicals, theimprovement that comprises conducting the reaction in the presence ofelemental platinum deposited on gamma alumina, as catalyst.

11. In the process for the production of vinyl trichlorosilane involvingthe reaction of acetylene with trichlorosilane, the improvement thatcomprises conducting the reaction in the presence of platinum depositedon gamma alumina, as catalyst.

12. In the process for the production of vinyl trichlorosilane involvingthe reaction of acetylene with trichlorosilane, the improvement thatcomprises conducting the reaction on a continuous basis in the presenceof platinum deposited on gamma alumina, as catalyst. v

13. In the process for the production of organosilicon compounds thatcomprises reacting an unsaturated aliphatic hydrocarbon withtrichlorosilane containing in excess of one percent by weight ofdichlorosilane, the improvement that comprises catalyzing the reactionwith platinum-gamma alumina.

14. In the process for the production of organosilicon compounds thatcomprises reacting an unsaturated aliphatic hydrocarbon with a mixtureof trichlorosilane and dichlorosilane, the improvement that comprisescatalyzing the reaction with platinum-gamma alumina.

15. In the process for the production of ethyl trichlorosilane anddiethyldichlorosilane by reaction of ethylene with a mixture ofdichlorosilane and trichlorosilane, the improvement that comprisescatalyzing the reaction with platinum deposited on gamma alumina.

16. In the process for the production of ethyl trichlorosilane byreaction of ethylene and trichlorosilane, the improvement that comprisescatalyzing the reaction with a catalyst consisting of platinum on gammaalumina.

References Cited in the file of this patent UNITED STATES PATENTS2,632,013 Wagner et al. Mar. 17, 1953 2,637,738 Wagner May 5, 19532,658,028 Haensel et al Nov. 3, 1953 FOREIGN PATENTS 44,934 Russia Nov.30, 1935 UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTION PatentNos 2,851,473 September 9, 1958 George H. Wagner et a1.

It is herehfi certified that error appears in the -printed specification1 of the above numbered patent requiring correction and that the saidLetters Patent should read as corrected below.

Column 6, line 33, for "up to 2.50 C. read up to 350 C. columns 7 and 8,Table VII, third column thereof, third line from the bottom, for "ClCI-1CH:3H read ClCH -CH=CH i Signed and sealed this 12th day of July 1960.

(SEAL) Attest:

KARL H, AXLINE ROBERT C. WATSON Attesting Officer Commissioner ofPatents

1. IN A PROCESS FOR THE PRODUCTION OF ORGANOSILICON COMPOUNDS THATCOMPRISES REACTING AN UNSATURATED ORGANIC COMPOUND CONTAINING AT LEASTONE NON-AROMATIC MULTIPLE CARBON TO CARBON BOND WITH A SILANE CONTAININGAT LEAST ONE SILANIC HYDROGEN BOND, THE IMPROVEMENT THAT COMPRISESCATALYZING THE REACTION WITH PLATINUM-GAMMA ALUMINA.